Water → HCID 19434326, compound

HRID 1735720Notes

Reaction equation

HRID 1735720 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].Br[CH2:24][CH2:25][CH2:26][Cl:27].O>CN(C=O)C.C(OCC)(=O)C>[Cl:27][CH2:26][CH2:25][CH2:24][N:7]1[C:8]2[C:13](=[CH:12][C:11]([CH2:15][N:16]3[CH:20]=[CH:19][N:18]=[CH:17]3)=[CH:10][CH:9]=2)[CH:14]=[C:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropane2×HCID 24758Sodium hydrideHCID 19434338HCID 19434338, compound

Product 1

HCID 19434326HCID 19434326, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Ethoxycarbonyl-5-(1H-imidazol-1-ylmethyl)-1H-indole (1.00 g) was dissolved in DMF (10 ml), and thereto was added sodium hydride (156 mg, purity 60%) under ice-cooling, followed by stirring at room temperature for 1 hour. Thereto was added 1-bromo-3-chloropropane (0.39 ml ), and the mixture was stirred for 1.5 hours. 1-Bromo-3-chloropropane (0.20 ml) was added again, and the mixture was stirred at room temperature for 16 hours. Water and ethyl acetate were added to the reaction mixture for extraction, followed by washing with saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (Daisogel 15 g, elution; CHCl3 --CHCl3 /MeOH=50/1-30/1) to give 1.26 g of an oily substance (1). IR (Neat, νcm-1) 1710, 1700, 1520, 1470 1H-NMR (CDCl3, δ ppm) 1.40 (3H, t, J=6.6 Hz, CH2CH3 ), 2.29 (2H, m, CH2CH2Cl), 3.63 (2H, t, J=6.0 Hz, CH2Cl), 4.38 (2H, quart, J=6.6 Hz, CH2CH3), 4.72 (2H, t, J=6.0 Hz, NCH2), 5.20 (2H, s, C5--CH2), 6.70-7.85 (7H, indole H, imidazole H)

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1.5 hours
  3. stirringthe mixture was stirred at room temperature for 16 hours
  4. washby washing with saturated brine
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (Daisogel 15 g, elution; CHCl3 --CHCl3 /MeOH=50/1-30/1)

Sources & evidence

ORD record
ord-b0029e190b61419e8a7212559ca447cf
Source dataset
uspto-grants-1996_07
Patent number
US05538973

Reaction notes

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